Resentment typically carries a notorious reputation and is often painted as a negative emotion that impedes communal peace, as it traps its victims to the past. The stigma against resentment, broadly conceptualized as a politicized form of anger, can be attributed to the influence of Nietzsche’s ressentiment. Nevertheless, certain forms of resentment are acknowledged by philosophers as valid reactions to legitimate moral infractions. Resentment, they argue, is intrinsically tied to one’s notion of self-respect and moral values. In this paper, I argue that, while standard accounts of resentment may be theoretically cogent when applied to singular and individual issues, these accounts are not conceptually adequate enough to apply to the complexities of collective and structural problems. Focusing on colonial resentment, I argue that resentment ought not to be vilified insofar as it can be a pivotal and instrumentally valuable tool for marginalized people to engage in what Coulthard calls “self-affirmative praxis.” This is because resentment, as a dual expression of love for oneself and the other, not only helps colonized subjects avoid the internalization of hatred and violence, but it also helps them detect and aim to fix injustices, as resentment has vital information about justice, fairness, and boundaries.